


The Challenge

by felicityollies



Category: Arrow (TV 2012)
Genre: Aftercare, BDSM, Biting, Cunnilingus, Dom/sub, F/M, Frottage, Oral Sex, Pink Panties, Plot What Plot/Porn Without Plot, Shameless Smut, Smut, Spanking, Teasing
Language: English
Status: Completed
Published: 2017-02-14
Updated: 2017-02-14
Packaged: 2018-09-24 12:02:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,129
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9725273
Author URL: https://archiveofourown.org/users/felicityollies/pseuds/felicityollies
Summary: smut-a-thon prompt:  “You look real good in that suit/dress/skirt/outfit.”





	

**Author's Note:**

> I decided to take this in a different direction or at least somewhat of a direction that I haven’t written before. It’s probably not everyone’s cup of tea.

Never dare Oliver to do anything unless you’re serious because he will do it. He could never let a challenge evade him. It might have been childish, but he really couldn’t care less. Besides, it was fun. Especially when the challenges were issued by the love of his life.

Felicity liked to play games. This wasn’t a secret by any means. These games could range from seeing who could go longer without finishing to her tying him up. Both of which he thoroughly enjoyed. He loved to please her. The need to make her happy in whatever way possible was etched into his very being.

He loved her and he loved her games, so he would do what she asked.

The challenge that lie ahead for him sat in a delicate little box on their bed. It was white, wrapped with a pink ribbon, which was tied neatly on top with a little bow. A note with perfectly written letters in green ink sat just beside it. _“You know what to do ;)”_ was all it said.

He licked his lips and took the box into his hand. Carefully, he undid the ribbon, pulling the box open. 

This was something that he had never done before, but oh did he want to. Not only because it would make Felicity happy, but because he was always up for expanding his horizons when it came to things of a sexual nature.

He pulled a small amount of fabric from the box. Bright pink and lacey, just enough to cover him, but it wasn’t like anyone other than Felicity was going to see him. He took his pajamas and his boxers off, so that he could slide it on. The fabric was soft against him, cupping him gently. A thin length of fabric slid between his cheeks. It felt weird, very weird, but he was determined to meet his fiancee’s challenge. He was going to wear it all damn day.

His grey suit was smooth, every button in order, the handkerchief and tie perfectly set, and his shoes shined. He looked like he always did when he went to work; professional and ready to perform his duties as mayor.

It was easy to go about his day as if nothing was out of the ordinary. A few hours in he almost forgot he was even wearing it. After getting used to it, it was down right comfortable. He had to stop himself from letting his mind wander, though. His thoughts quickly turned to whether or not this particular pair was actually Felicity’s. It would explain why it was somewhat tight. The idea that he was wearing her thong was even more of a turn on. He couldn’t help it. It felt good to wear them; he couldn’t explain why, but he liked it. He liked the idea that they weren’t brand new off the shelf and that Felicity had worn them. Was it weird? He didn’t give a damn.

Around noon she texted him asking for a picture. He bit his lip in thought. Glancing around, he didn’t hear anyone or see anyone. His office was completely quiet. But he wasn’t going to take a picture of what was underneath his suit. Instead, he sent her a dorky selfie.

She replied quickly with, “You know that’s not what I meant.”

He chuckled, typing “I know,” and hitting send.

“Teasing is only going to get you punished.”

He read those words and swallowed hard. As much as he loved to please her, he also loved to tease and toe the line. Her punishments were never too harsh, no they were just right.

With a shaky breath, he replied, “Oh well.”

The only response he got was an angry devil emoji. Oh, it was going to hurt so good. He thought about it all day. Imagining what kind of plans Felicity had in store for him. He had meetings to go to and work to focus on, but his mind was completely in the gutter. It made not getting hard at work a little more complicated, but how could he keep his attention on Mayoral duties when his very sexy soon-to-be wife was planning to make a night of this too.

To make matters worse it seemed that he wasn’t going to get out of there on time. He did not want to keep Felicity waiting for very long.

By the time he was walking through the door it was dark out and he was more than ready to get into bed with Felicity.

“You’re late,” a light flicked on in the living room, “You know I don’t like it when you’re late.”

That tone she used. So commanding and strong, it made his cock twitch in his pants.

“I would get in here quickly if I were you,” she snapped.

He closed and locked the door before practically sprinting into the living room. When his eyes fell on her he gulped. She sat in her favorite chair, legs crossed and on display for him to see. Blood red pumps with heels that were slightly pointed. A short and very tight black dress that hugged her curves and showed off her shoulders.

“Shit,” he whispered.

She knew just how to make him melt. Her eyes moved over him, drinking him in. He felt a shiver go up his spine. She looked at him like she was ready to devour him. And he was going to let her.

“You look real good in that suit,” she purred, “But I want to see what’s underneath.”

His hands went for his belt, but she raised a hand to stop him.

“But not just yet,” she pushed herself up from the chair. She stood tall in front of him, reaching out to take his tie into her hand, “I think we should take this into the bedroom.”

“Yes,” he breathed out, leaning closer.

Their lips were suddenly only an inch or two apart. He leaned in the rest of the way to kiss her, but she pulled back.

“You just keep adding onto your punishment,” she hissed.

Shit. He knew he wasn’t supposed to do anything without her permission.

“At this rate you may never get an orgasm tonight,” she stepped away from him, but motioned for him to follow her.

He swallowed back a whimper. There was no way he was going to complain, though. He did this to himself. If he hadn’t been teasing her, if he hadn’t been late, if he hadn’t tried to kiss her without permission then maybe this scenario would play out differently. He knew he was still going to enjoy it because he loved everything she did, but still.

In their bedroom, she sat down on the edge of the bed. “Strip,” she commanded.

He nodded, “Yes, Felicity,” he worked the buttons on his suit jacket and shrugged it off.

His eyes never left hers as he removed every last piece of clothing, except for the lacy pink thong of course.

She licked her plump red lips at the sight. It made him swallow again. With one finger she motioned him forward.

“Sexy,” she whispered as her hand ghosted over his semi-hard cock, “Did you wear it all day?” she asked.

He nodded, “I did,” he wanted so badly for her to touch him, but he managed to keep himself still.

“Did you like it?” a smirk pulled at those perfect lips, “Did you like wearing my panties,” she slipped one finger under the side strap, “They seem a little tight.”

He had to bite back a groan.

“Well?” she snapped the fabric against him.

“Yes, I loved it.”

“Good,” she stood and walked around him.

Her fingers moved over his back and then down to his ass. She gripped onto his cheek and looked up at him. “Mmm, I just want to bite you,” she giggled.

“Please,” he whined.

“Please what?” she asked.

“Please, bite me, Felicity.”

She gripped him a little hard, watching his face. “No,” with that she gave him a hard smack.

He almost pouted, but he knew she wasn’t going to do anything that he wanted. Not yet.

“Tell me what have you done to deserve anything?” she walked around to his front again.

He opened his mouth, but immediately snapped it shut.

“Exactly,” she suddenly gripped his cock through the fabric. Holding him much harder than necessary. It hurt, but he liked it. “Let’s see if you can earn it.”

He nodded enthusiastically.

“Words,” he squeezed.

He gasped, “Yes, Felicity,” he choked out the words.

She let go with a smirk, “First of all… you had better not make a mess in my panties,” she tugged at the fabric, making snap against him again.

“Never,” he shook his head.

He was already getting harder and they barely started. The thong was tight on him to begin with, not so much so that it was uncomfortable, but the harder he got the more his dick pressed into the fabric. There wasn’t enough stretch, no leeway at all, which meant he was confined in a lacy pink prison.

He liked it.

“Second,” she moved back from him and hiked up her dress, “Make me feel good,” she sat down on the edge of the bed again.

He didn’t need telling twice. In seconds, he was down on his knees in front of her. He lifted her legs, so she could swing them over his shoulders. Her sharp heels dug into his back, but he didn’t complain. The pain felt good. He leaned in close to her pussy. Her scent invaded his nose and made him groan. She was already so wet. Her pussy glistened with need. He pressed his tongue flat to her swelling clit.

“No teasing,” she dug her heel into him harder.

“Yes, ma’am,” he took her clit into his mouth and sucked roughly.

“God,” she moaned.

He smirked as he let go, delving lower. His tongue lapped up her sweetness, swallowing everything like he hadn’t drank or eaten in weeks. He swirled the wet muscle at her entrance before pressing inside. Probing her walls, he elicited more noises from her. Her fingers gripped onto his hair and pushed him harder into her pussy.

He was trying desperately to focus on pleasuring her, but he could feel his cock twitch, aching to be touched. The tightness of the panties rubbed up against him, making it more difficult to not lose control. He had a will of steel and strong stamina, but that didn’t mean he had moments of weakness.

Oliver was more than a little determined to keep it together.

“Oh fuck,” she moaned out louder.

His nose rubbed against her clit as he continued to press against her walls. He could feel her starting to clench and tremble. She pulled his hair when she came, shouting while he drank the juices that flowed around his tongue. Felicity panted and relaxed. She stroked his hair gently for a couple seconds.

He knew then that he had pleased her.

“May I kiss you?” He asked, looking up at her.

“You may,” she relaxed against the bed for a moment.

He pressed a kiss to her pussy, to those sweet lips, and to her swollen clit. When he pressed his lips to her thigh, though, she reached down to grip him by his hair and tug him upward.

“That’s enough,” she stated firmly. She let go and moved her hand to grip his chin. “You’re a mess now,” she chuckled. “You like being covered, don’t you?”

“I do, I love it.”

“Good.”

She pushed him back and stood again. “Stand up straight,” she commanded.

He immediately jumped to his feet. As soon as he did his very obvious problem was on display for her to see. He was straining painfully against the cloth.

“Well, look at that,” she said with another smirk, “You really do enjoy it.”

Felicity dragged one finger up his length. He shuddered, closing his eyes and counting to ten. There was no way he was going to lose it right now.

“Now what is that?”

His eyes snapped open and he looked down.

Her thumb moved across his head, rubbing teasingly, and spreading his precum. Shit.

“I believe I said specifically not to make a mess, did I not?”

He nodded, “You did. You did.”

“Then why did you do it?” she pulled her hand away from him only to slap him hard across the face.

He winced. “I’m sorry, Felicity.”

“You will be,” she snapped, “Get onto the bed. On all fours.”

Without hesitation he crawled up onto their bed. He would be lying if he said that the slap hadn’t turned him on even more. Felicity climbed up behind him and smacked his ass hard again. He groaned quietly.

“I could fuck your ass so good,” she muttered, “But that would be too good for you today.”

She smacked him again.

“Are you disappointed?” she asked.

He nodded, but quickly remembered his words. “Yes.”

Another smack. “I guess you should have thought of that earlier.”

“Yes, Felicity.”

Three more smacks before she finally stopped. “Now look at this swollen red cheek,” she said softly.

Without warning she sunk her teeth into him. He hissed in both pain and surprise. But he loved it when she did that. She left perfect teeth marks every time, marking him as hers. It wasn’t necessary because he was hers. He always had been and always would be. That didn’t mean he wanted her to stop.

When she pulled back, she dragged her tongue across the spot, “I love this ass,” muttered before giving one last smack.

“Thank you,” he choked out.

“Mhmm,” she hummed, “Now roll over. Onto your back. Now.”

He moved and lay back, happy that he could see her again. The way she was watching him made his cock twitch again. God he was so hard. He needed to cum, but he knew it wasn’t going to happen easily.

She climbed up on top of him, straddling his chest. “Grab the headboard,” she ordered, “Hold onto it and keep your hands there.”

He gripped onto it, knowing that he wasn’t going to be allowed to touch her any time soon.

“Good boy,” she rolled her hips forward, dragging her wet pussy across his abs.

“Fuck,” he moaned.

Her dress was lifted enough that he could see her beautiful pussy. She rolled her hips again, rubbing herself against him. It only took him a moment to realize that she was going to get off on his abs and that was unbelievably sexy. She was just high enough that she wasn’t going to touch his cock. Oh it was torture.

He held onto the underside of the headboard tightly. His knuckles were starting to whiten. She kept her body moving. Her eyes right on his face.

“Oh fuck,” she moaned loudly, “I’m going to cum all over you.”

He gritted his teeth, trying not to come undone, but it was becoming almost impossible.

“Can you feel it?” she asked, grinding her clit into his muscles.

“Yes,” he whined.

“You’re not going to cum without permission, are you?” she gripped onto his sides, digging her nails into him.

“No!”

“I don’t believe y-you… oh god,” she rubbed herself even harder.

Her body trembled on top of him as she hit her climax.

Oliver muttered under his breath and shut his eyes.

“Look at me,” she panted.

He looked at her, biting down on his lip so hard he thought it might bleed. It was the only thing that kept him from completely blowing his load.

Felicity slowed down and took a moment to catch her breath. She lifted herself and inspected him. His stomach was wet from her, but he had kept himself together.

“Oh you were a good boy,” she smiled, “Should I let you cum?”

He nodded, barely able to find his voice, “Please.”

“Do you want to cum by my hand?” she cupped his balls.

He shook his head, “No.”

“By my mouth?”

“No, please, Felicity,” he begged.

“Tell me what you want?”

“Fuck me! Please.”

She smirked and finally moved the panties off of his body. Kicking away her heels and tugging off her dress, she moved to straddle him again.

“Touch my clit,” she demanded as she slid down onto him roughly.

His hands flew forward, he touched her clit, rubbing it as she moved her body. The warmth that enveloped him made him shudder and groan. He wanted to hold on just a little bit longer. God he needed to cum, but he wanted to savor the feeling of being inside of her. He knew he wasn’t going to get his wish, not with the way she was moving her body, and then as she reached a third climax it was all over.

Her walls squeezed him, pulling him deeper inside of her. He felt his balls tighten, “Fuck!” he shouted.

His cock throbbed and he spilled his cum inside of her. Felicity’s body milked him for all he was worth, prolonging the already intense orgasm. His trembling body finally started to slow. He lay back in bed, panting heavily.

Felicity slid off of him and moved to lie down beside him. They stayed quiet for a few moments as they caught their breath.

Then she moved even closer to him, “How you’re feeling?” she asked, kissing his chest between soft pants.

He swallowed thickly, trying to find his words again. His head was swimming and his body was buzzing with pleasure.

“Oliver?”

“I’m good. So good,” he breathed out.

She giggled so innocently, “I’m glad,” she kissed up to his lips, “You did so well.”

He smiled against her lips, “Mmm it felt awesome.”

She wrapped her arm around him and tangled her legs with his. “I didn’t think you were going to do it.”

“You dared me,” he said, snuggling close her.

“I did not, I said ‘Oliver you would look sexy in my underwear’ and you said ‘Okay’ and that was the end of that,” she laughed.

Her hands moved over his arm and side, gently caressing him, making him feel loved and wanted. Letting him know that he had done a good job and that she was pleased with him. It made him want to hum with happiness. He felt so sated in more ways than one.

“I’m pretty sure there was an ‘I bet you won’t do it’ in there somewhere,” he said.

“Hmmm… maybe there was,” she smiled and kissed him softly, “I’m tired now.” 

“Me too,” he mumbled, kissing her again, “Nap and then food?”

“And then shower. You’re a mess.”

He snorted, “I believe that is your fault.”

“Maybe,” she giggled again.

**Author's Note:**

> Let me know what y'all think!


End file.
